Phosphoric Acid → N-(6-methylthioquinolin-5-yl)-2-bromodecanamide

HRID 2257190Notes

Reaction equation

HRID 2257190 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=O.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[C:30]([S:31][CH3:32])=[CH:29][CH:28]=[C:27]2[C:22]=1[CH:23]=[CH:24][CH:25]=[N:26]2.OP(O)(O)=O>CN(C=O)C.C(Cl)Cl.C(OCC)(=O)C>[CH3:32][S:31][C:30]1[C:21]([NH:20][C:3](=[O:5])[CH:2]([Br:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[CH:25][CH:24]=[CH:23]2

Participants

8

Reactant 4

HCID 1004Phosphoric AcidHCID 65578Oxalyl chlorideHCID 983102-Bromodecanoic acidHCID 103976605-Amino-6-methylthioquinoline

Product 1

HCID 19027925N-(6-methylthioquinolin-5-yl)-2-bromodecanamideYield 62.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-bromodecanoic acid (184 mg, 0.73 mmol) in CH2C12 (3.0 ml) was injected by syringe oxalyl chloride (0.06 ml, 105 mol %) and then DMF (1 drop). After stirring at room temperature for 1 hour, N-methyl morpoline (0.24 ml, 300 mol %) was added. To this mixture was injected a solution of 5-amino-6-methylthioquinoline (139 mg, 100 mol %) in CH2Cl2 (2.0 ml). After stirring at room temperature for an additional 30 min. the reaction mixture was diluted with CH2Cl2 (30 ml), poured over 1.0M H3PO4 (100 ml), and extracted with CH2Cl2 (3×30 ml). The combined extracts were dried (Na2SO4), evaporated, and chromatographed using 1% triethylamine:ethyl acetate as eluants to give the title compound (192 mg, 62% yield).

Workup

  1. additionN-methyl morpoline (0.24 ml, 300 mol %) was added
  2. stirringAfter stirring at room temperature for an additional 30 min. the reaction mixture
  3. extractionextracted with CH2Cl2 (3×30 ml)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customevaporated
  6. customchromatographed

Sources & evidence

ORD record
ord-5faf4540dabc4edf95c76e26bea1716b
Source dataset
uspto-grants-1997_08
Patent number
US05656634

Reaction notes

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